Author: AOLGeneration

[M]y happy New Year with a Younger, [F]un Partner

New Year’s Eve 1999-2000 I attended a house party with a college friend of mine and his younger cousin. I was 22 at the time. My friend was a couple of years older than me, but his cousin was four years younger. His cousin brought along two gals with him from his high school class. One was his girlfriend (or someone he was ‘seeing’). The other was her single friend, Tiffany.

Well, I learned two things early on: (1) Tiffany is into me and wants to hook up; and (2) this New Year’s Eve is also her 18th birthday. She was an attractive gal in a severe sort of way – very sharp facial features with sandy blond hair. Her body seems nice but it is hard to tell based upon the type of cocktail dress she wore and the fact that she had on tights. I actually had reservations about hooking up with Tiffany because it just seemed so convenient that she was turning 18 on New Year’s Eve. Read more »

[M]y tryst with sister’s [F] college roommate

After I graduated college I lived at home for a year while working at my first job. My sister was a freshman in college. She had her roommate visit over Thanksgiving break along with several other friends she had made. Something clicked between us. It was unspoken – I could just tell by the way she looked at me that she saw me as more than her college roommate’s brother, but as a possible sexual partner. An impression I did not get from any of the other friends of my sister there. Fortunately, the roommate was actually staying at our house. The other friends were either local or staying at other houses with local friends. Read more »

A friend’s fix-up leads [M]e to hook up with three [F]’s.

Because this story involves not one but three women (all of whom know each other), and is very detailed, to protect their anonymity I am going to use initials instead of first names.

This journey starts off in late 1995, a friend who came from the same hometown as me set me up with her younger sister who I will call “K.” K was still in high school but 18. K had very pretty, cat-like eyes and large breasts. During winter break back in our hometown, we went to a movie and back to her (and my friend/her sister’s) house. We go into K’s room, shut the door, and talk on her bed for a while. Finally, I make a move. It is well-received. We mainly kiss but eventually K’s top and bra come off and I am treated to feeling and sucking some awesome, pendulous 18 y o breasts.

I am really into K. She visits my friend/her sister at our college a month or two later. I make time to visit with her but am crestfallen to learn that she is dating someone her own age in high school. No big deal – we behave like adults, awkwardness is avoided, and we remain friends. Read more »

[M]y hook-up with the nicest [F] I’d had the pleasure to meet

Aside from my wife, who is the nicest person I know, I thought it might be fun to recount the most kind-hearted woman I was ever sexual with.

I was in college at the time. It was my senior year. I met a girl at a fraternity party who (for the sake of anonymity) had a name that started with “M”. She was 2 years younger than me, and I could tell she was pleasantly plump. By no means obese, just a bigger girl yet with curves in the right places. She was with a girl who had a rare skin disorder in which her pigmentation became very splotchy from the merest exposure to the sun. It was impossible for M’s friend to avoid this condition even in the cold weather town our college was located. Merely going to class and back would be enough to trigger this condition.

There was nothing objectionable about M. She had a cute face, normal disposition, and it was clear that she had other friends, but wanted to take a friend out at night who might not always get a chance to enjoy the typical bar-going college lifestyle. Read more »

The one time a [F] fingered [M]y my asshole

I once met a cute, red-haired BBW off of AOL. We met at a local diner, and after we ate I asked her if she’d like to go back to my place, to which she said ‘sure.’ We technically had sex on this first date. However, I used a condom, and I never had much success with condoms. In this instance, I managed to get it on and get inside of her, but the rubber robbed me of all sensation and I lost my erection shortly thereafter.

After our failed attempt at intercourse, I went down on her (for a second time). She came from oral and wanted to return the favor. She blew me, gave me a handjob, but I was having a hard time cumming that night. But she was not accepting of defeat. She said, “I know what you need,” and before I could say, “What’s that,” BAMM, in goes her index finger into my asshole. She wiggled it around in a very confident, almost authoritative manner, jerked my cock with her other hand, and inside of 20 seconds I was spurting rope after rope of semen all over my abdomen and upper chest.

Working as a fundraiser in college, out of the blue, I [M] lucked into a wholly unexpected hook-up with a younger, prude [F] student coworker.

My senior year of college I worked as a student fundraiser at a phone bank where we solicited donations to our school from alums and parents of current students. On break, I overheard a 19 year old sophomore girl mention to another coworker that she had to take the bus back to her apartment. I had a car that year, so later on I went up to her and offered to give her a ride back to her place instead of her having to take the bus. She seemed so appreciative of my offer and relieved not to have to take the bus that I hazarded to turn it into a date and asked to take her out to dinner before taking her home. She was totally game; I took her to a casual yet quality French bistro near the phone bank where we worked. It was a good call because in getting to know each other I learned of our shared appreciation of foreign films, especially French films. She seemed interested in me romantically, but she was formal and seemingly inexperienced. For my three previous years in this college, I typically met experienced gals. Everything they were doing with me, they had done before with plenty of other guys and would do again next weekend with plenty more. In other words, sluts. This girl seemed different. Still, I figured I’d roll the dice and ask her back to my apartment where I had the French classic, The Discreet Charm of the Bourgeoise (1972), rented. Sure enough, she was interested in coming back to my place after dinner to watch it. I figured if I was very lucky with this girl I might get to finger her. Read more »

When I [M] was 22, a 29 y o [F] mother of two fucked me.

I met her at a bar while out with friends. She was on a blind date and came up to me for me to ‘save her’ from this guy. I don’t know if that was true or if she just wanted to go up to me, but I got her number. We went out twice before (just light petting, kissing and I fingered her). I had absolutely no idea she was a mom. Then on the third date, we met at a restaurant so we both had our cars. It was on this date that she told me about her situation as we hung out in her Jeep Grand Cherokee. I told her that while I really liked her I did not think it would be fair to lead her or her kids on. I was just too young; I knew it. I wasn’t going to marry a mom w/2 kids from a previous marriage, so I thought the most civil thing to do would be to break things off then and there. She was tearful; I felt awful. She asked me if I would go in the backseat with her for a little while before we parted ways. I didn’t think it was a good idea, but I figured it wouldn’t hurt to kiss her goodbye. Read more »